1. Field of the Invention
The present invention relates to a novel benzothiazole derivative having the following general formula (I), ##STR3## in which R.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, halogen, straight and branched (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8) halogenoalkyl or (C.sub.1 -C.sub.8)alkoxy,
X represents N or CH, PA1 Y represents a group -OR.sup.4, -SR.sup.5 or ##STR4## and R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently of one another represent hydrogen, straight and branched (C.sub.1 -C.sub.16)alkyl, (C.sub.3 -C.sub.8) alkenyl, (C.sub.3 -C.sub.8)alkynyl, (C.sub.3 -C.sub.8)cycloalkyl, alkyl substituted with C.sub.1 -C.sub.6)alkoxy or (C.sub.1 -C.sub.6)halogenoalkyl, or represent a substituted phenyl, phenylacyl or benzyl group wherein the possible substituent on the phenyl, phenylacyl or benzyl group includes halogen, straight and branched (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)alkoxy, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, phenoxy, nitro, cyano and a five- or six-membered heterocyclic group containing one to four nitrogen atoms. PA1 X represents N or CH, PA1 Y represents a group -OR.sup.4, -SR.sup.5 or ##STR9## and R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently of one another represent hydrogen, straight and branched (C.sub.1 -C.sub.16)alkyl, (C.sub.3 -C.sub.8) alkenyl, (C.sub.3 -C.sub.8)alkynyl, (C.sub.3 -C.sub.8)cycloalkyl, alkyl substituted with (C.sub.1 -C.sub.6)alkoxy or (C.sub.1 -C.sub.6)halogenoalkyl, or represent a substituted phenyl, phenylacyl or benzyl group wherein the possible substituent on the phenyl, phenylacyl or benzyl group includes halogen, straight and branched (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)alkoxy, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, phenoxy, nitro, cyano and a five- or six-membered heterocyclic group containing one to four nitrogen atoms. PA1 (a) a compound of formula (VI) is substituted with a halogen and then reacted with an alkyl or acyl halide under basic condition to obtain a compound of formula (VII), PA1 (b) the compound of formula (VII) is subjected to a halogen-lithium substitution reaction and then reacted with dimethyloxalate to obtain a compound of formula (VIII), and PA1 (c) the compound of formula (VIII) thus obtained is reacted with methoxylamine under basic condition or subjected to a Wittig reaction with a phosphorus ylide, ##STR11## in which R.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, halogen, straight and branched (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)halogenoalkyl or (C.sub.1 -C.sub.8)alkoxy, PA1 X represents N or CH, PA1 R.sup.6 and R.sup.7 independently of one another represent hydrogen, straight and branched (C.sub.1 -C.sub.16)alkyl, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkylnyl, (C.sub.3 -C.sub.8)cycloalkyl, alkyl substituted with (C.sub.1 -C.sub.6)alkoxy or (C.sub.1 -C.sub.6)halogenoalkyl, or represent a substituted phenyl, phenylacyl or benzyl group wherein the possible substituent on the phenyl, phenylacyl and benzyl group includes halogen, straight and branched (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)alkoxy, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, phenoxy, nitro, cyano and a five- or six-membered heterocyclic group containing one to four nitrogen atoms, and PA1 Hal represents a halogen atom. PA1 (a) a compound of formula (VI') is diazotized with sodium nitrite and then substituted with a halogen to obtain a compound of formula (IX), PA1 (b) the compound of formula (IX) is reacted with an alcohol under basic condition to obtain a compound of formula (X), and PA1 (c) the compound of formula (X) is subjected to a halogen-lithuim substitution reaction and then reacted with dimethyloxalate to obtain a keto ester which is then reacted with methoxylamine under basic condition or subjected to a Wittig reaction with phosphorus ylide, ##STR12## in which R.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, halogen, straight or branched (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)halogenoalkyl or (C.sub.1 -C.sub.8)alkoxy, PA1 X represents N or CH, PA1 R.sup.4 represents hydrogen, straight and branched (C.sub.1 -C.sub.16)alkyl, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, (C.sub.3 -C.sub.8)cycloalkyl, alkyl substituted with (C.sub.1 -C.sub.6)alkoxy or (C.sub.1 -C.sub.6)halogenoalkyl, or represents a substituted phenyl, phenylacyl or benzyl group wherein the possible substituent on the phenyl, phenylacyl and benzyl group includes halogen, straight and branched (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)alkoxy, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl. phenoxy, nitro, cyano and a five- or six-membered heterocyclic group containing one to four nitrogen atoms, and PA1 Hal is a halogen atom. PA1 X represents N or CH, PA1 R.sup.5 represents hydrogen, straight and branched (C.sub.1 -C.sub.16)alkyl, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, (C.sub.3 -C.sub.8)cycloalkyl, alkyl substituted with (C.sub.1 -C.sub.6)alkoxy, or (C.sub.1 -C.sub.6)halogenoalkyl, or represents a substituted phenyl, phenylacyl or benzyl group wherein the possible substituent on the phenyl, phenylacyl or benzyl group includes halogen, straight and branched (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)alkoxy, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, phenoxy, nitro, cyano and a five- or six-membered heterocyclic group containing one to four nitrogen atoms, and PA1 Hal is a halogen atom.
The present invention also relates to a process for preparation of the benzothiazole derivative of formula(I), as defined above, and the use of the benzothiazole derivative(I) for combating phythopathogenic organisms and fungi present on animal.
2. Background Art
In 1977, Anke et. al. (J. of Antibiotics 30, 806 (1977)) have reported strobillurin A having a potent and broad-spectrum microbicidal activity: ##STR5##
Thereafter, many studies for providing numerous compounds analogous to strobillurin A have been made.
In 1987, European Laid-open Patent Publication No. 299694 (Cliff, et. al.) has disclosed the compound of formula (III) having a potent microbicidal activity against various fungi, particularly against apple scab causative organism (Venturia inaequalis), grape downy mildew causative organism (Plasmopara viticola) etc. ##STR6##
In addition, numerous analogous compounds including the compound of formula (IV) disclosed in German Laid-open Patent Publication No. 3,939,258 (Klausener, 1989) and the compound of formula (V) disclosed in European Laid-open Patent Publication No. 480,798 (Benoit), both of which are bicyclic compounds similar to the compound (I) according to the present invention and have been reported as having a potent microbicidal activity, have been developed. ##STR7##
On the basis of the above mentioned prior art, the present inventors have prepared numerous strobillurin A analogous compounds and studied their microbicidal activities. As a result, we have found that a certain compound having a benzothiazole derivative as the lipophilic group exhibits potent broad-spectrum microbicidal activity against phythopathogenic organisms and fungi present on animal.
Therefore, it is an object of the present invention to provide a novel benzothiazole derivative of formula(I), as defined above, which has a potent broad-spectrum microbicidal activity.
It is a further object of this invention to provide a process for preparing the novel benzothiazole derivative of formula(I).
It is a further object of this invention to provide a use of the novel benzothiazole derivative of formula(I) for combating phythopathogenic organisms and fungi present on animal.
The foregoing has outlined some of the more pertinent objects of the present invention. These objects should be construed to be merely illustrative of some of the more pertinent features and applications of the invention. Many other beneficial results can be obtained by applying the disclosed invention in a different manner or modifying the invention within the scope of the disclosure. Accordingly, other objects and a more thorough understanding of the invention may be had by referring to the disclosure of invention, in addition to the scope of the invention defined by the claims.